(S)-3-[(4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-3-hydroxy-2-(4-methoxy-benzenesulfonylamino)-propionic acid benzyl ester | 607403-12-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-3-[(4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-3-hydroxy-2-(4-methoxy-benzenesulfonylamino)-propionic acid benzyl ester
• CAS: 607403-12-3
• 化学式: C₂₉H₄₃NO₉SSi
• 分子量: 609.813
• InChiKey: VPHNZYLEMDBDGC-QYIJMHBESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.99
• 重原子数：
  41.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  129.62
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (S)-3-[(4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-3-hydroxy-2-(4-methoxy-benzenesulfonylamino)-propionic acid benzyl ester 在 palladium on activated charcoal 吡啶 、 Dowex-H⁺ 、 四丁基氟化铵 、 氢气 、 sodium methylate 、 1-羟基苯并三唑 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (2R,3S,4R,5S)-3,4,5-trihydroxy-1-(4'-methoxybenzenesulfonyl)-piperidine-2-carboxylic acid hydroxamide
  参考文献：
  名称：

  Design, synthesis and evaluation of novel azasugar-based MMP/ADAM inhibitors

  摘要：

  In order to verify whether azasugar would be a useful scaffold for inhibitory activity against metalloproteinases, we synthesized some azasugar-based compounds. As a result, it is clarified that azasugar moiety could function as successful inhibitor of matrix metalloproteinase-1, -3 and -9 and TACE. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00531-6
• 作为产物：
  描述：

  (4R,5S)-5-tert-butyldimethylsilyloxymethyl-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde 、 (4-Methoxy-benzenesulfonylamino)-acetic acid benzyl ester 在 lithium diisopropyl amide 、 tin(ll) chloride 作用下， 以65%的产率得到(S)-3-[(4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-3-hydroxy-2-(4-methoxy-benzenesulfonylamino)-propionic acid benzyl ester
  参考文献：
  名称：

  Design, synthesis and evaluation of novel azasugar-based MMP/ADAM inhibitors

  摘要：

  In order to verify whether azasugar would be a useful scaffold for inhibitory activity against metalloproteinases, we synthesized some azasugar-based compounds. As a result, it is clarified that azasugar moiety could function as successful inhibitor of matrix metalloproteinase-1, -3 and -9 and TACE. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00531-6